Outkast, “B.O.B.”

Outkast greeted the 21st century with a single that’ll probably sound ahead of its time in the 22nd. Big Boi and André 3000 were inspired by hearing the hard, double-time rhythms of drum-and-bass music at a London party. “There wasn’t anything in hip-hop that was killing me at the time,” André said. “But that shit was tough … I thought about how to Americanize it.” With an insane beat, Hendrix-at-Monterey guitar and massed voices chanting like a gospel choir conducted by Afrika Bambaataa, “B.O.B.” became one of the greatest left-field hits of all time.

Grandmaster Flash and the Furious Five, “The Adventures of Grandmaster Flash on the Wheels of Steel”

“I was just one big human sampler,” Joseph “Grandmaster Flash” Saddler once said of his groundbreaking record-mixing technique. And the Grandmaster never cut faster than on the record that established the hip-hop DJ as a new kind of pop musician. Flash’s days as a DJ date back to 1974, when he and other kids who were too young to get into discos began playing at house parties and block parties in their South Bronx neighborhoods. He was also an electronics geek who eventually came up with his own unique setup: using three turntables, a crossfader (a device he helped pioneer) and his own grab bag of frenetic moves. On “The Adventures of Grandmaster Flash on the Wheels of Steel,” 23-year-old Flash created a continuous party jam by splicing, scratching and, in a sense, reinventing records – “the short, climactic parts that really grabbed me,” he recalled. Chic, Blondie and Queen all make appearances in the mix, and Flash even threw in early rap hits by Spoonie Gee and his own crew, the Furious Five. Self-promotion never sounded so smooth.

Marley Marl was hip-hop’s first superproducer, a master of the chopped-and-looped soul sample and a huge influence on sound painters from RZA to Dr. Dre. On “The Symphony,” he dialed up a beat for the ages – a ferocious drum break and a snatch of Otis Redding piano – and summoned the cream of his Juice Crew affiliates. The result: a truly great late-Eighties posse cut. Smoothest flow: Big Daddy Kane. Sharpest couplet: Kool G Rap (“Making veterans run for medicine/’Cause I put out more lights in a fight than Con Edison.”) MVP: Marley Marl.

Funky 4 + 1, “That’s the Joint”

“That’s the joint” captures the essence and energy of hip-hop’s party-hearty early glory days: nearly 10 minutes of exhortations and boasts, sprawling across a hopped-up disco beat. By today’s standards, the braggadocio is quaint – “We got rhymes on our minds, we got rockin’ in our heart” – but the rappers can flow, and the bass breakdown, by four-string god Doug Wimbish, is as funky as anything this side of Bootsy Collins. The real star of the show, though, is the Funky 4’s “plus-one woman,” Sha-Rock (a.k.a. Sharon Green), the first female MC featured on a hit rap record.

Salt-N-Pepa, “Push It”

Salt-N-Pepa’s signature jam was one of the first rap records to top the dance charts, and it remains a classic party-starter. The electro groove is a monster, and the refrain distills the message of half the songs ever written in nine indelible words: “Push it! Push it good! Push it real good!” Cheryl “Salt” James and Sandra “Pepa” Denton weren’t technical virtuosos, but they trounce all comers. “Back then, there weren’t many women,” Pepa recalled. “We were raw, we were bold, we were in your face with it. We did not care!”

Lauryn Hill, “Lost Ones”

The opening track on Lauryn Hill’s landmark solo debut is a reminder of how viciously this great singer could rhyme. It was recorded in Jamaica, and Hill raps (and, in the chorus, croons) in her version of a Trenchtown patois. “It’s funny how money changes situations,” she begins, but what follows isn’t funny: a spit-roasting indictment of arrogance, greed and spiritual blindness. The song’s alleged target – Hill’s former bandmate in the Fugees and ex-lover Wyclef Jean – must have been quaking in his Timbs.

De La Soul, “Me Myself and I”

Urged by their label to provide their adventurous 1989 debut album, 3 Feet High and Rising, with a song that wouldn’t be “so over someone’s head,” De La Soul concocted a cosmically inclusive house-party jam. Their eclectic Daisy Age style got them labeled hip-hop hippies, but it elevated a whole movement of Native Tongues groups like A Tribe Called Quest and the Jungle Brothers: “We are going back to the Sixties,” Posdnuos said in 1989. “But also to the Seventies, the Fifties, the Eighties and on into the future.”

Audio Two, “Top Billin'”

Rhyming over nothing but the drum break from the Honey Drippers’ “Impeach the President” (brilliantly flipped by co-producer Daddy-O), Kirk “MC Milk Dee” Robinson thanks his parents, brags about his bodyguard and shouts-out both his Bed-Stuy hood and his DJ brother/partner Giz. He also invites rappers to “Bite a rhyme/If you dare.” Plenty did: Variations on the hook – “Milk is chillin’, Gizmo’s chillin’/What more can I say? Top billin’!” – have been spit by gazillions of MCs, from Dre to Biggie to Jay Z.

Boogie Down Productions, “South Bronx”

Kris “KRS-One” Parker of Boogie Down Productions was rap’s original righteous teacher, and this funky-fresh story of hip-hop’s early days is a required master class. DJ Scott La Rock threads a no-nonsense James Brown sample, and KRS recalls a late-Seventies golden age of jams in the park and innovators like Afrika Bambaataa and Kool Herc. Sadly, the same year “South Bronx” was released, La Rock (born Scott Monroe Sterling) was shot while trying to break up a fight, ending one of Eighties hip-hop’s most promising careers.

2Pac feat. Dr. Dre and Roger Troutman, “California Love”

On his biggest hit, 2Pac celebrated his recent release from prison (“Fresh outta jail, California dreamin'”) with a “serenade [to] the streets of L.A.” It was Dre’s beat, though, that brought the sunshine: a buoyantly funky party groove, with delicious vocoder vocals from the legendary Roger Troutman. “The whole city was in pandemonium,” recalled Kendrick Lamar, who was perched on his father’s shoulders while he watched Dre and Pac shoot the song’s video. “I think since that day I was inspired, subconsciously, to be an artist.”

Kurtis Blow, “The Breaks”

The first rap hit on a major label, peaking at Number 87 on Billboard’s Hot 100, was a no-frills joint: a loping bass line and jumping beat with the Harlem-born Blow presiding over playground-party noises and percussion breakdowns. Blow toured extensively behind “The Breaks,” introducing America to B-boy culture – “something I’m sure few people outside New York have ever seen,” he said in 1981 – while blazing a trail for rappers like Run of Run-DMC, who started out calling himself “The Son of Kurtis Blow.”

Eminem, “My Name Is”

“God sent me to piss the world off,” announced Eminem – and by the time the curtain dropped on his debut single, he’d fulfilled his mission. It was a sound no one had heard before: a white rapper from a Midwestern trailer park with a seemingly bottomless supply of uproarious rhymes. Over Dr. Dre’s cartoon-funk beat, Em tears off Pamela Anderson’s breasts, goes after his junior high English teacher’s testicles with a stapler and rhymes “head straight” and “impregnate.” “If you’re sick enough to think it,” he said at the time, “then you’re sick enough to say it.”

Missy Elliott, “Get Ur Freak On”

“Me and Timbaland been hot since 20 years ago,” crows Elliott, a ludicrous boast that seemed almost plausible in the late Nineties and early Aughts, when the pair were music’s most reliable brainbenders. “Get Ur Freak On” is Missy and Tim at their funkiest and nuttiest. The production takes hip-hop Orientalism to outer space, marshaling Indian tablas and snatches of Japanese speech. “When it blew like that, I realized there was a whole other part of the world that people were ready for,” she said. “It was a good thing.”

Outkast, “Rosa Parks”

The song that made the world fall in love with Outkast brought earthy Southern flavor to the rap charts. Big Boi and André 3000’s party rhymes were deceptively deep, and their flow was smoother than Georgia molasses. As for Rosa Parks: She felt the lyrics made light of her heroism and brought a lawsuit against the group. “We never intended the song to be about Rosa Parks,” André told Rolling Stone at the time. “It was just symbolic, meaning that we were comin’ back out, so all you other MCs move to the back of the bus.”

Ice Cube, “It Was a Good Day”

Ice Cube’s biggest hit is a ghetto pastorale, forsaking violence to revel in good vibes and a plush Isley Brothers sample. “I rap all this gangsta stuff,” he later said. “What about all the good days I had?” Cube eats a fine breakfast, smokes his homeys on the basketball court and smokes some chronic with a girl. He even looks up to see “the lights of the Goodyear blimp/And it read, ‘Ice Cube’s a pimp.'” Recently, the Internet went nuts trying to nail down the actual date of Cube’s good day – but it’s obviously a fairy tale, with its own happily-ever-after ending. As Cube said himself, “It’s a fictional song.”

Mobb Deep, “Shook Ones (Part II)”

In the mid-Nineties, Mobb Deep came out of New York’s Queensbridge projects and boiled East Coast gangsta rap down to its rawest, nihilist essence. A suspense-amping snippet from a Quincy Jones soundtrack infuses the rumbling song with a sinister hiss, while background mumbles add shady menace. Prodigy, whose mother was a member of Sixties girl group the Crystals, promises that his “gunshots will make you levitate,” and makes sure to remind listeners that he’s “only 19.” Years later, you still ache for that kid.

Schoolly D, “P.S.K. What Does It Mean?”

“This birthed gangsta rap,” Questlove said. “N.W.A just took this formula and ran with it.” The Philly rapper’s 1985 joint takes its name from a local gang, Park Side Killers, and its wicked “Sucker MCs”-style beats from an evidently stressed-out Roland 909 drum machine. In a lazily menacing flow, Schoolly buys coke, parties with a hooker, buys weed and goes to the club, where he finds an MC biting his style. “Put my pistol up against his head,” he matter-of-factly explains. That he decides not to pull the trigger makes the jam no less chilling.

Jay Z, “99 Problems”

Rick Rubin hadn’t worked on a hip-hop project for years when Def Jam’s Lyor Cohen persuaded him to get in the studio with Jay Z. “I knew I was gonna get fresh shit,” Cohen recalled. He got one of the most explosive tracks ever, based around the gigantic drums from Billy Squier’s “The Big Beat.” Jay concocts an indelible pop chorus and sketches out a scene based on an encounter with a racist cop from his pre-stardom days. “The first offense wasn’t the crack in the ride but the color of the driver,” he wrote in his memoir.

Kanye West, “Jesus Walks”

Kanye West has never been shy about his God complex, but humility, not hubris, drives hip-hop’s greatest gospel testimonial. The production is stirring – a church choir cresting above a martial beat – and West has a message to match, forsaking easy pieties to rap about internal struggle (“We at war with ourselves”) and self-doubt (“I want to talk to God, but I’m afraid because we ain’t spoke in so long”). The song helped solidify his own transcendent status: “I made ‘Jesus Walks,'” West rapped years later on “Otis.” “I’m never going to hell.”

Nas, “N.Y. State of Mind”

No track better sums up Nas’ ability to spin dense, dazzlingly lucid verses. “N.Y. State of Mind,” a highlight of his hugely important 1994 debut, Illmatic, is no anthem or ode to the city. It’s a detailed narrative about a Gotham gunfight, delivered in a nearly 60-bar run that was later broken up to create a spellbinding track. “He did the whole first verse in one take,” recalled producer DJ Premier, who exactingly balanced two jazz samples for the muted, moonlit beat. “He stopped and said, ‘Does that sound cool?’ And we were all like, ‘Oh, my God!'”

The Notorious B.I.G., “Hypnotize”

Notorious B.I.G’s first Hot 100 chart-topper, which hit Number One just weeks after his March 1997 murder, is his supreme pop-rap moment: a litany of boasts and threats, delivered with cool sangfroid over Puff Daddy’s Herb Alpert-sampling candy-corn beat. It was a fitting epitaph, a testament to Biggie’s inimitable flow, matchless wordplay and knack for leavening gangsta sex and violence with punch lines even a toddler could cuddle up to. “Such a likable guy,” said Jay Z. “He’s forever loved by hip-hop.”

LL Cool J, “Mama Said Knock You Out”

“Don’t call it a comeback!” begins rap’s hottest-ever comeback. After finding crossover success in the late Eighties, LL Cool J returned to street-fighting hip-hop – pledging to “bash this beat like a skull” and returning fire from Kool Moe Dee’s diss record “How Ya Like Me Now?” The beat, one of legendary producer Marley Marl’s finest tracks, rides the four-count chant from Sly and the Family Stone’s “Trip to Your Heart,” and the track peaks with LL repeating “Damage! Damage! Damage!” like he’s done rhyming and is ready to break shit. Point made.

Eminem, “Lose Yourself”

Eminem’s biggest hit ever plays like Rocky condensed into a five-minute song. It helped that in telling the story of Rabbit – the trailer-dwelling aspiring rapper he played in 8 Mile – Eminem was writing autobiographically, sidestepping demented hijinks and pure rage in favor of tough realist rhymes about overcoming very long odds. Em cut the song during a brief break from filming. “He came in and laid down all three verses in one take,” said engineer Steven King. “Jaws dropped – we were like, ‘Oh, my God! This story has been building in him.'”

Craig Mack has faded into obscurity – reportedly renouncing rap to join a fundamentalist Christian cult in South Carolina – but he left his mark with the remix of his debut single. Mack’s verse has its moments – “I wanna grab my dick/Too lazy/Hold it for me” – but labelmate Biggie Smalls drops a true classic, opening his freestyle with “Niggas is mad I get more butt than ashtrays.”

A Tribe Called Quest feat. Leaders of the New School, “Scenario”

Q-Tip, Phife Dawg and Ali Shaheed Muhammad made their reputation as jazz-influenced bohemian innovators, but their best song is a full-on B-boy shout-along. For many hip-hop heads, this summit meeting between A Tribe Called Quest and Leaders of the New School is hip-hop’s greatest posse cut. The breakout performance comes from 19-year-old upstart Busta Rhymes, who emerges roaring like a dungeon dragon. “I thought he was it,” Q-Tip said later. “I just wanted to set him up.”

Big Daddy Kane, “Ain’t No Half-Steppin'”

When Jay Z christened Brooklyn’s Barclays Center with an eight-show run, he only brought out one guest: Big Daddy Kane. And for good reason: Antonio Hardy was the killer wordsmith of hip-hop’s golden age. On “Ain’t No Half-Steppin’,” his tone is rich and commanding as he rocks tightly coiled, extended metaphors over Marley Marl’s laidback groove: “Rappers, you better be/Ready to die because you’re petty/You’re just a butter knife, I’m a machete.” Legend has it even Rakim turned down a challenge to go mic-to-mic with Kane.

Rob Base and DJ E-Z Rock, “It Takes Two”

“All I know is, it’s a club banger,” Rob Base said. Mixing hip-hop and dance music, lifting liberally from James Brown background singer Lyn Collins’ 1972 song “Think (About It),” Base and DJ E-Z Rock’s irresistible 1988 smash was a pop-rap landmark and an ode to understanding and respect that brought people together under a groove. The song was produced by Teddy Riley, who deployed a similar jump-up syncopation as the king of New Jack Swing. Base later said, “I wanted people to get up and dance and not have to worry about fightin’ and arguin.'”

Eric B. and Rakim, “I Know You Got Soul”

“When I’m writing I’m trapped between the lines/I escape when I finish the rhyme,” explains Rakim, rocking the sort of jam that disappeared once copyright lawyers stepped up their game. Eric B. built this landmark 1987 track by looping a chunk of the James Brown-produced song of the same name (recorded in 1970 by Bobby Byrd and the J.B.’s). But turnabout is fair play: British mixmasters M/A/R/R/S built their hit “Pump Up the Volume” around a sample of Rakim saying that phrase on “I Know You Got Soul.”

EPMD, “Strictly Business”

The best thing about EPMD’s inaugural single is the duo’s self-produced beat – a cornucopia of blatant samples from the golden age of artistic pilfering, with Eric Clapton’s “I Shot the Sheriff” busting wildstyle moves on the floor next to Mountain and Kool and the Gang. Erick Sermon and Parrish Smith’s laid-back rhymes were revolutionary, too. Most rappers in 1988 were still stuck on the brash cadences that town criers from LL Cool J to Chuck D favored; EPMD’s casual, goofy approach to the mic laid the groundwork for generations of chilled-out MCs.

LL Cool J, “Rock the Bells”

Leaping off a hard-rock riff from AC/DC’s “Flick of the Switch” (also tapped for the Beastie Boys’ “Slow and Low”), Long Island teenager James Todd Smith calls out every rapper in town, disses Michael Jackson and Prince, dismisses Bruce Springsteen and pledges to “make Madonna scream.” The third single from his 1985 debut is Rick Rubin’s remix of an early 12-inch version that, in fact, had bells. But this one rings even louder. It’s a rap Rosetta Stone quoted to this day. LL liked it so much he sampled it himself on 1991’s equally crushing “Mama Said Knock You Out.”

50 Cent, “In Da Club”

“We just made some shit we wanted to hear,” producer Dr. Dre said. “As soon as 50 walked in the studio, he picked up a pen and we were done in an hour.” Queens native Curtis Jackson had it all: an almost mythic backstory (he was a talented thug who’d once taken nine bullets), the backing of Dr. Dre and Eminem and a lush, languid flow. All he needed was a monster beat; over clinically precise handclaps and synths, he sent America hurtling toward the dance floor while threatening to “put the rap game in a choke hold.” By the time this hit Number One, he had.

Beastie Boys, “Paul Revere”

Michael “Mike D” Diamond remembers when Adam “MCA” Yauch hit on the squishy beat that propels this crackling single – by running the tape backward. “We were as giddy as kids, yelling in the studio,” Diamond says. “It was the simplest idea, and he killed it.” One rhyme about a girl and “a Wiffle ball bat” got them in hot water for misogyny. The Beasties would back off from that kind of verse as they matured on records and Yauch turned to Buddhism. But they performed “Paul Revere” right to the end: at Bonnaroo in 2009, Yauch’s last show before his death in 2012.

2Pac, “Dear Mama”

“The emotional, the sad songs, were his personal favorite,” recalled 2Pac producer Johnny J. His 1995 ballad tribute to his mother, Afeni Shakur, is the ne plus ultra of hip-hop mom songs. Tony Pizarro’s beat sets a tender mood, and 2Pac strikes a similar note: “I appreciate how you raised me/And all the extra love that you gave me.” But “Dear Mama” hits harder for its realism, especially when Pac raps about his mother’s struggles with drug addiction: “And even as a crack fiend, Mama/You always was a black queen, Mama.”

Run-DMC, “Peter Piper”

The greatest ode ever to the Midas-like powers of a DJ. Jam Master Jay sliced up composer Bob James’ 1975 smooth-jazz nugget “Take Me to the Mardi Gras” as Run and DMC dropped nursery-rhyme science in summing up their partner’s greatness: “He’s a big bad wolf in your neighborhood/Not bad meaning bad but bad meaning good!” Run-DMC’s label, Profile Records, wanted the MTV-ready rap-rock Aerosmith collaboration “Walk This Way” to be the first single off their 1986 album, Raising Hell. But the group was adamant that “My Adidas/Peter Piper,” anthems of hip-hop culture, be the first release; Darryl “DMC” McDaniels later recalled saying, “If ya’ll don’t do it, we’re gonna give it to the radio and fuck everything up.” They prevailed, and Raising Hell became rap’s first blockbuster album. When Jam Master Jay (born Jason William Mizell) was shot and killed in 2002, Run-DMC immediately retired. They’d eventually reunite again in 2012, with Jam Master Jay’s two sons as part of the group.

Jay Z feat. UGK, “Big Pimpin'”

Jay Z has since claimed that he’s a little ashamed by the rawness of his tricky verses on “Big Pimpin’ .” “I thug ’em, fuck ’em, love ’em, leave ’em/’Cause I don’t fuckin’ need ’em,” he boasts. “What kind of animal would say this sort of thing?” Jay said of his own lyrics. “Reading it is really harsh.” But “Big Pimpin'” is the ultimate playa anthem, radiating excess and power. Jay defied North-South regional bias by reaching across the Mason-Dixon to give Port Arthur, Texas, duo UGK a prominent spot on one of his biggest hits. His guests’ nimble wordplay added a brilliant twist to the track: “Go read a book, you illiterate son of a bitch, and step up your vocab,” taunted Bun B. Timbaland’s beat fit the ecumenical vibe perfectly – a bugged-out orchestral sample lifted from a 1957 song by Egyptian singer Abdel Halim Hafez that gave Jay Z’s supersize boasts a perfect sense of world-straddling dominance.

N.W.A, “Fuck tha Police”

The pivot point between Public Enemy’s Black Panther revivalism and gangsta rap’s nihilism, this 1988 hard-funk assault indicted the LAPD and seemed like prophecy in the Rodney King/L.A. riots era. “Fuckin with me cuz I’m a teenager/With a little bit of gold and a pager,” rhymes a 19-year-old Ice Cube, adding, “When I’m finished, it’s gonna be a bloodbath of cops/Dyin’ in L.A.” The FBI took it seriously enough to send a warning letter to the group’s label that alleged the song “encourages violence against, and disrespect for the law enforcement officer.” The publicity established N.W.A as hip-hop’s bad boys and made the song an agit-pop anthem for the ages. “Peace is a fiction to me,” Ice Cube told Rolling Stone in 1989. “We deal with reality. Violence is reality. When you say something like that, it scares people. You’re supposed to picture life as a bowl of cherries. But it’s not.”

Public Enemy, “Rebel Without a Pause”

Opening with a Jesse Jackson sample (“Brothers and sisters, I don’t know what this world is coming to!”) and upping the ante with Chuck D’s broadcaster-baiting (“Radio/Suckers never play me”), this 1987 single perfected Public Enemy’s hand-grenade attack and set the stage for their seminal It Takes a Nation of Millions to Hold Us Back. Its siren squeal is actually a looped horn from the 1970 J.B.’s jam “The Grunt Pt. 1”; the groove bites James Brown’s “Funky Drummer”; and Terminator X scratches the chorus of Chubb Rock’s “Rock and Roll Dude.” (“We use samples like an artist would use paint,” said producer Hank Shocklee.) When Chuck D heard the finished recording, he was so blown away he announced, “I could die tomorrow.”

Doug E. Fresh and Slick Rick, “La-Di-Da-Di”

Eye-patched British-American rapper Slick Rick was still known as MC Ricky D when “La Di Da Di” was released in 1985. Rick spins a rude tale of being hit on by his ex-girlfriend’s mom, while beatbox pioneer Fresh provides backdrop. A milestone in rap storytelling and product placement (name-checking Gucci, Bally, Kangol, Polo, Johnson’s Baby Powder and Oil of Olay), it would be referenced endlessly – most famously in the chorus of Notorious B.I.G.’s “Hypnotize.” It also started the trend of rappers breaking into off-key song. “La-Di-Da-Di” began as a live routine that turned into a sensation. “Doug E. used to carry me around with him,” Rick recalled. “The crowd … first they would look at you like, ‘Whatever, skinny nerd trying to get put on,’ but then when you kicked the humor and they got to laughing and enjoying themselves, it sold itself.”

Pete Rock and C.L. Smooth, “They Reminisce Over You (T.R.O.Y.)”

Hip-hop has produced many classic elegies – from Ice Cube’s “Dead Homiez” to Bone Thugs-N-Harmony’s “Tha Crossroads.” Pete Rock and C.L. Smooth’s “They Reminisce Over You” is as beautiful as they come. The early-Nineties duo wrote the song for their Mount Vernon, New York, pal “Trouble” T-Roy, a dancer with Heavy D and the Boyz who died while on tour in 1990. C.L. Smooth came up with his lyrics before Pete Rock had produced the track, which is hard to imagine since they fit together so perfectly. Over a tender, sky-blown sax sample from Sixties jazz-pop composer Tom Scott, C.L. Smooth spins a tribute to his fallen friend into a vivid celebration of family (literal, metaphorical and musical) that’s as much free-roaming backyard-barbecue toast as somber funeral speech. “When we listened back to the record, we just started crying,” Pete Rock recalled. “When I felt like that, I was like, ‘This is it.’ Deep in my heart I felt like this was gonna be something big.”

Wu-Tang Clan, “C.R.E.A.M.”

Part of what made the Wu-Tang Clan so great was their messy, multitudinous sprawl. “When we started recording Enter the Wu-Tang, the whole group was usually there for every session; sometimes it felt like their whole neighborhood was in the studio,” recalled Ethan Ryman, an engineer on the group’s landmark 1993 debut. “Every now and then, RZA and I would have to clear the room so we could get to the equipment.” Yet the finest song on the album is ruthlessly efficient: just two breathless verses, plus the catchiest acronym-based hook in history, laying out the rules of street capitalism. RZA’s sampled pianos rattle like the wind down a project alleyway as Raekwon and Inspectah Deck trade harrowing war stories (“No question I would speed for cracks and weed/The combination made my eyes bleed”). It’s not a romantic portrait, but it does have a happy ending, when Rae joins the Clan: “Figured out I went the wrong route/So I got with a sick-ass clique and went all-out.”

Eric B. and Rakim, “Paid in Full”

Exhibit A in the case for Rakim as hip-hop’s John Coltrane. His incandescent thought-bubble rap on “Paid in Full” is all iced flow and sly beat-dodging, a good-versus-evil meditation that calmly frames thug life inside real-life economics (an appetite for “a nice big plate of fish/Which is my favorite dish”) and a novelist’s eye for detail (“Ain’t nothin’ but sweat inside my hand”). In an era when most hip-hop songs exploded with loud, over-the-top boasting, Rakim’s relatable, low-key flow was game-changing. “I always wanted to kind of make the listener feel like it was them that I was talking about, or to the point that I could say the rhyme and feel like it’s them saying it,” he said years later. Eric B.’s beat, looped from a break on “Ashley’s Roachclip” by the Soul Searchers, is just as groundbreaking; it inspired the British DJ team Coldcut to craft “Paid in Full (Seven Minutes of Madness),” which soon became the song’s definitive version, and arguably the dopest remix in hip-hop history.

N.W.A, “Straight Outta Compton”

“A murder rap to keep you dancin’ with a crime record like Charles Manson,” the explosive first track on N.W.A’s 1988 debut kicked off the gangsta-rap era with a raw menace like nothing anyone had heard before. Ice Cube, Dr. Dre, MC Ren, DJ Yella and Eazy-E shifted rap’s focus from New York to South Central Los Angeles despite MTV’s refusal to air the video for “Compton” due to its violent imagery. “Kids were just waiting for it,” said Bryan Turner of Priority Records, which quickly sold 2 million copies of Straight Outta Compton. One of those kids was a young Chris Rock, who brought a copy from L.A. to play for his dumbfounded friends on the East Coast. “[N.W.A] was like the British Invasion for black people,” Rock said.

The Notorious B.I.G., “Juicy”

The greatest rapper who ever lived, at his absolute peak: hilarious, incisive and insanely inventive as he balances urban realism (“Birthdays was the worst days”) and playalistic excess (“Now we sip champagne when we’re thirsty”). The funky first single from the Notorious B.I.G.’s world-smacking 1994 debut, Ready to Die, was a departure from the rugged East Coast rap sound of his 1993 debut single, “Party and Bullshit,” and a far cry from the gangsta-don image he originally wanted to project. But executive producer Sean “Puffy” Combs insisted Big flow over a simple, club-friendly loop of Mtume’s early Eighties dance-party jam “Juicy Fruit.” (Producer Pete Rock says Combs got the idea from him.) “I wanted to release music that let people know he was more than just a gangsta rapper,” Combs said later. “He showed his pain, but in the end, he wanted to make people feel good.”

Public Enemy, “Fight the Power”

Hank Shocklee, one half of Public Enemy’s production team the Bomb Squad, said the group wanted their track for Spike Lee’s explosive 1989 movie Do the Right Thing to have a “defiant, aggressive, I’m-not-gonna-take-it feeling.” They nailed it. No band since the Sex Pistols had pushed pop music’s sonic and political possibilities as far as Public Enemy did on “Fight the Power.” Chuck D blasted “straight-up racist” institutions like Elvis, John Wayne and the U.S. Postal Service, as the Bomb Squad spun layer upon layer of samples (James Brown, the Dramatics, Uriah Heep) into implosive war-dance funk. Chuck D came up with the song’s concept while on tour with Run-DMC in Italy, and Lee directed its frenetic protest-themed video, which was filmed on the streets of Bed-Stuy, Brooklyn. The result was the total in-your-face package. In the summer of ’89, it seemed like it might start a full-on revolution.

Dr. Dre feat. Snoop Doggy Dogg, “Nuthin’ but a ‘G’ Thang”

Climbing to Number Two on the single charts in early 1993, “Nuthin’ But a ‘G’ Thang” made Dr. Dre the undisputed king of West Coast hip-hop, while ushering the genre into the mainstream and seriously challenging New York’s cultural dominance. The irresistibly catchy song’s secret weapon was a relatively unknown 21-year-old pup named Snoop Doggy Dogg, whose verses are packed with effortless quotables. ” ‘ G’ Thang” also introduced Dre’s masterful “G-Funk” style of production, which updated George Clinton’s Seventies legacy with slow, rubbery grooves and layered synth hooks. “We made records during the crack era, where everything was hyped up, sped up and zoned out,” Chuck D explained. “Dre came along with ‘G’ Thang’ and slowed the whole genre down. He took hip-hop from the crack era to the weed era.” Take a listen to 21st-century inheritors, from Kendrick Lamar to Future, and it’s pretty clear we’re living in his weedy world.

Geto Boys, “Mind Playing Tricks on Me”

Shortly before the Geto Boys released their 1991 album, We Can’t Be Stopped, the Houston trio’s diminutive member Bushwick Bill was shot in the eye during a suicidal freakout. He survived; a photo of him displaying his wound appeared on the album’s cover. This Top 30 hit, recorded before but issued after the incident, revealed even more of the manic depression and death wish deep inside the Geto Boys’ violent, misogynist rhymes. Scarface, who wrote and produced the track, sounded like his movie namesake: hopped-up and fully armed at the edge of sanity, over dark-treble guitar and a gunslinger-walk rhythm sampled from Isaac Hayes’ soundtrack to the 1974 film Three Tough Guys. In a genre where fear was not thought manly, “Mind Playing Tricks on Me” was a classic of cracked ghetto armor and bloody surrender: proof that even the hardest of the hard have worried hearts.

Run-DMC, “Sucker M.C.’s”

In the beginning, hip-hop was club music, an offshoot of disco usually meant for dancing and partying. After “Sucker M.C.’s,” it belonged to teenagers on the street. “There was never a B-boy record made until we made ‘Sucker M.C.’s,’ ” declared the late Run-DMC DJ Jam Master Jay. Sure enough, the 1983 track – nothing but rhymes and scratches over hard Oberheim DMX beats and hand claps – seemed designed specifically with break dancers in mind. “Sucker” was conceived as a B-side throwaway to the group’s debut, “It’s Like That,” but its whiplash groove and everydude rhymes were even more radical. Run charts his creation myth, disses competitors, brags about his Caddy and his girl appeal. Then his partner introduces himself with “I’m DMC in the place to be/I go to St. John’s University!” Indeed: A new school had arrived. “I wasn’t afraid to rap about school being cool,” Darryl “DMC” McDaniels said years later. “That was empowering. That’s the legacy when people look at Run-DMC.”

Afrika Bambaataa and the Soulsonic Force, “Planet Rock”

“One of the most influential songs of everything,” says Rick Rubin. “It changed the world.” Helmed by a reformed South Bronx gang member turned punk-mystic community leader/DJ, with help from superstar producers-in-the-making Arthur Baker and John Robie, this 1982 atom bomb interpolated parts of Kraftwerk’s “Trans-Europe Express” and “Numbers,” mating synth stabs with robotic MC chants (“Rock rock to the planet rock/Don’t stop!”) on a futurist jam that circled the globe. It introduced Roland 808 beats to hip-hop, for which acts from the Beasties to Kanye West would be grateful. Just as important, it coined the sonic language of electro, Detroit techno, freestyle R&B, Miami bass and Brazilian favela funk – in other words, much of modern dance music. “At the time, we barely considered it a rap record,” adds Rubin. “It was more about a new sound.” In the words of Chuck D of Public Enemy, “There hasn’t been a song like it in hip-hop since.”

Sugarhill Gang, “Rapper’s Delight”

It took three guys from New Jersey to put hip-hop, a still-underground New York-born phenomenon, on Top 40 radio for the first time. Bronx DJ Grandmaster Flash recalled hearing “Rapper’s Delight” on the air and asking, “The Sugarhill who? Who are these people?” Sugar Hill Records founder Sylvia Robinson got the idea for the song while watching a DJ talk over a record in a Harlem club, and she formed the Sugarhill Gang shortly thereafter. On the original 12-inch single, “Rapper’s Delight” was 15 minutes of urban-playboy bragging over a disco-rhythm track that blatantly quoted the bass line in Chic’s 1979 hit “Good Times.” Chip Shearin, who played bass guitar at the “Rapper’s Delight” session, recalled “sweating bullets” as he played the song’s body-moving lick, without changes or mistakes, for a quarter-hour. Shearin, then 17, was paid $70. Chic’s Nile Rodgers and Bernard Edwards did much better, eventually getting writer credits and royalties after threatening legal action.

Grandmaster Flash and the Furious Five, “The Message”

“The Message” was a total knock out of the park,” says Chuck D of Public Enemy. “It was the first dominant rap group with the most dominant MC saying something that meant something.” It was the first song to tell, with hip-hop’s rhythmic and vocal force, the truth about modern life in inner-city America. Over seven minutes, atop a Seventies P-Funk jam, rapper Melle Mel and co-writer Duke Bootee, a member of the Sugar Hill Records house band, traded lines and scenes of struggle and decay, with a warning at the end of each verse: “Don’t push me ’cause I’m close to the edge/I’m trying not to lose my head.” The Furious Five’s pioneering DJ Grandmaster Flash later said that “The Message” proved their music could “speak things that have social significance and truth.” Yet, when they first heard Bootee’s demo (originally titled “The Jungle”), they were worried that hip-hop clubgoers would not dig the subject matter and slowed-down beat. As Melle Mel recalled, he was the member who “caved in” and agreed to record it. Sugar Hill Records head Sylvia Robinson got him to write and rap more lyrics, and Sugar Hill studio player Reggie Griffin added the indelible synthesizer lick. Despite being credited on the record, Flash and the Five appeared only in a closing skit, in which they’re harassed and arrested by police. “The Message” was a hit, but its messy birth was fatal to the Five, who soon split up. Their most notable reunion was in 2007, when they were the first rap group inducted into the Rock and Roll Hall of Fame.